Enhanced diastereoselectivity via confinement

Photoisomerization of 2,3-diphenylcyclopropane-1-carboxylic acid derivatives within zeolites

J. Sivaguru, Raghavan B. Sunoj, Takehiko Wada, Yumi Origane, Yoshihisa Inoue, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

From the perspective of asymmetric induction, the photochemistry of 24 chiral esters and amides of cis-2,3-diphenylcyclopropane-1-carboxylic acid from excited singlet and triplet states has been investigated within zeolites. The chiral auxiliaries placed at a remote location from the isomerization site functioned far better within a zeolite than in solution. Generally, chiral auxiliaries with an aromatic or a carbonyl substituent performed better than the ones containing only alkyl substituents. A model based on cation-binding- dependent flexibility of the chiral auxiliary accounts for the observed variation in de between aryl (and carbonyl) and alkyl chiral auxiliaries within zeolites. Cation-dependent diastereomer switch was also observed in select examples.

Original languageEnglish
Pages (from-to)6533-6547
Number of pages15
JournalJournal of Organic Chemistry
Volume69
Issue number20
DOIs
StatePublished - Oct 1 2004
Externally publishedYes

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Zeolites
Photoisomerization
Carboxylic Acids
Derivatives
Cations
Photochemical reactions
Isomerization
Amides
Esters
Switches
diphenylcyclopropane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enhanced diastereoselectivity via confinement : Photoisomerization of 2,3-diphenylcyclopropane-1-carboxylic acid derivatives within zeolites. / Sivaguru, J.; Sunoj, Raghavan B.; Wada, Takehiko; Origane, Yumi; Inoue, Yoshihisa; Ramamurthy, Vaidhyanathan.

In: Journal of Organic Chemistry, Vol. 69, No. 20, 01.10.2004, p. 6533-6547.

Research output: Contribution to journalArticle

Sivaguru, J. ; Sunoj, Raghavan B. ; Wada, Takehiko ; Origane, Yumi ; Inoue, Yoshihisa ; Ramamurthy, Vaidhyanathan. / Enhanced diastereoselectivity via confinement : Photoisomerization of 2,3-diphenylcyclopropane-1-carboxylic acid derivatives within zeolites. In: Journal of Organic Chemistry. 2004 ; Vol. 69, No. 20. pp. 6533-6547.
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